


Fucking Your Boss and Other Ways to Nearly Die

by cinderace



Category: Villainous (Cartoon)
Genre: Blood Play, Demon Dick, M/M, Oral Fixation, Self-Indulgent, Tentacle Dick, face riding, im so sorry Alan, later chapters probably gonna have piss stuff, so much wet pussy holy shit, trans!flug
Language: English
Status: Completed
Published: 2020-03-10
Updated: 2020-04-06
Packaged: 2021-03-01 02:27:17
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 3,992
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23087749
Author URL: https://archiveofourown.org/users/cinderace/pseuds/cinderace
Summary: Flug has always had a taste for the extreme.  Those extremes just happen to all involve his demon boss, Black Hat.
Relationships: Black Hat/Dr. Flug (Villainous)
Comments: 4
Kudos: 170





	1. Chapter 1

**Author's Note:**

> Alan don’t read this please.

It was another typical, slow day at the manor. Flug had just gotten Demencia to calm down by giving her a femur bone to chew on, as well as putting 5.0.5 down for a nap. Because of this, he was alone for a few hours. Which usually meant work, but not today. He wasn’t quite in the mood for work. He was more in the mood for...well...

The scientist kicked a leg up on his desk, fumbling with his jeans. He growled softly to himself before tugging his bag up a bit to get some better air. He worked them down to his knees before pushing a de-gloved hand into his boxers. He shivered slightly. 

“Damn you, Flug...look how wet you already are.” He scolded himself. It was true, the man was a soaked mess. He’d been thinking about the usual; his boss utterly destroying him. His middle finger traced his wet hole, making him jolt a little. 

The slender man brought his middle finger up to his clit, his juices coming along with it. He tensed up slightly, a small whine escaping his lips. He was ridiculously sensitive; usually, the smallest touch would make him tense up and moan. And today was no exception. He began to rub his clit in small circles, and he immediately relaxed. This was exactly what he needed, just a few minutes to destress. 

“Hmm~” He whined to himself. His pubic hair cling to his entrance a bit from the juices, but he didn’t care. Soon, his boxers were at his knees as well, and he was in absolute heaven. He closed his eyes as his breathing already grew a bit ragged. 

“O-Oh, Black Hat...” He murmured to himself. Imagining the eldritch tear into him. Use him. Make him bleed and scream. Everything about it just...thrilled him to the absolute core. His juices were starting to puddle onto his cold, metal chair by this point. He was shivering, breathing heavy, twitching, moaning. And he was oh, so close. 

“M-Mm~! Oh, o-oh, sir~! M-Mister Black Hat~!” He wasn’t even aware of his volume by this point. He was only focused on cumming. It was his only goal. Nothing mattered in that moment. He gripped his desk with one hand, the other was now being ground against by the desperate man. He’d given up on rubbing and was now just rutting his shaking hand. Nothing mattered. Nothing fucking mattered. 

“FLUG!”

Well, maybe one thing did. 

That cold voice immediately snapped him out of his daze. He sat up in a panic, quickly trying to work his boxers at the very least back on. 

“S-Sir-!” He squeaked. He fumbled with his jeans, still dazed from being snapped out of pleasure like that. 

“What the fuck are you doing when you should be working?!” Black Hat snarled. It wasn’t uncommon for the eldritch to just appear in various places in the manor. In fact, he loved to scare the members of his organization by just...standing and staring in the corner of the room. Today just happened to be a bad time for him to wanna scare the scientist. 

“I-It’s not what-“

“Save it! Don’t try to lie to me, Flug. You know I know damn well what you’re doing.” The demon was quick to cross the room, looming over the soaked scientist. Flug squeaked softly in fear. 

“I-I’m sorry, I-I won’t do it again during work hours! I promise!”

However, the demon didn’t seem...quite...as angry anymore. In fact, his expression was mostly blank. His forked tongue slithered out, almost...twitching? Was he smelling, Flug wondered? He got his answer pretty quick. 

“You smell amazing, doctor...” The demon murmured. His somewhat blank expression soon turned to one of lust, or perhaps mischief. Flug couldn’t quite tell. Flug swallowed. 

“Thanks...?” He asked, confused. How his boss went from being so angry to almost entranced, he didn’t quite know. He didn’t have much time to think on it, however, as his boss had now grabbed him by the wrist. The demon’s snake-like tongue was wrapping around his wet hand, smelling it. Flug shuddered a bit. His tongue was so hot and slimy, and wasn’t a feeling he was used to. It wasn’t a bad feeling by any means, just a new one. He peered up at Black Hat, completely frozen in fear. Those giant teeth, just centimeters from his flesh. The man could bite his hand off in one quick snap if he so chose to. This...this is what he wanted. He wanted his boss to absolutely terrify him in a sexual context. And it was right here, right now. 

“Shit...you’re a disgusting man, Flug. Masturbating instead of working. You’re vile.” Black Hat spoke, snapping Flug out of his thoughts. If the scientist could get more flushed...

“A-Ah, yeah...” He didn’t think his boss knew of him being trans. Did he know? Or did he just not care? Either way, he was happy his boss, the epitome of pure rot and evil, actually gendered him properly. 

“You don’t even deserve what I’m about to do to you. But, if it’ll get you to work again.” 

“H-Hm-?” Flug didn’t even get to finish that thought before his boss was on the move again. He let go of his hand, which was now soaked in both pussy juices and demon slobber, and began to work on his jeans. They slid off easily with the demon’s brute force. Then, off came his boxers. Black Hat nearly shredded them as he yanked them down. The cold air hit Flug’s crotch again, and the scientist yelped softly. The demon got on his knees and gripped Flug’s thighs tightly. His whole hand practically fit around Flug’s slender thighs. Black Hat’s piercing gaze was on Flug.

“Look at you...wet, throbbing mess. You’ve practically destroyed those boxers. I haven’t seen such a twitchy cunt in a long time.” Each word was a warm breath on Flug’s pussy, and he didn’t realize how badly he craved a sensation like that. Flug only nodded. 

“Y-Yes sir...” 

“Look at that clit of yours. It’s beautiful~” Black Hat’s voice was dripping with lust at this point. It only made Flug’s swollen clit twitch more. He shook his head. 

“It’s...just a micro penis pretty much, sir. Nothing too special. I wouldn’t recommend one.” Even in his terrified and horny stupor, he was still a little snarky and self-deprecating. The demon huffed. 

“Let me compliment you for once, Flug.” He leaned in, his tongue brushing Flug’s soaked entrance. Flug jolted hard, biting his knuckle to keep from making a pitiful noise. Black Hat smirked at his reaction. 

“I’m only smelling you. If you’ll react like that from just a simple touch, I can’t wait to see how you’ll react from having it buried deep in that cunt of yours~” He continued to praise the scientist as he lapped at his heated pussy, “You smell so fucking good~” 

Flug was in heaven. Watching his teeth draw close to the most sensitive part of his body was driving him wild. He bit down harder, shaking. 

“S...Sir...please...I-I need you s-so b...” He wasn’t even able to form a sentence properly. He was just getting so goddamn needy, and his boss knew it. After a few more moments of sniffing and teasing, Black Hat went in for the kill. Without so much as a warning. 

His hot tongue buried itself deep into Flug’s pussy in an instant, barely giving Flug time to react. He moaned out a little loudly, just staring down at the demon. The organ was much, much thicker than Flug thought it would be in him. Shapeshifting, he assumed? Either way, Flug was feeling pure ecstasy. 

And the demon’s teeth...god. They ever so softly grazed Flug’s flesh as Black Hat practically devoured his crotch. The scene would be horrifying to most, but to Flug, seeing those teeth just made him melt. The demon didn’t even need to move his tongue much before Flug came hard. 

Black Hat sneered, “Already, Flug? I don’t think so. I want you to actually focus on your work when we’re done here. Just a quick orgasm from tongue penetration isn’t going to cut it.” He growled. He moved up to Flug’s clit, his tongue toying with the sensitive nub. 

Flug was just along for the ride at this point. He was spaced out from hormones just rushing through his body. Hell, he could barely hear what his boss said between recovering from an orgasm and this overwhelming pleasure he felt. 

Black Hat pulled away to take a glove off with his teeth, casting it aside. At first, Flug was confused, but it hit him fast. His boss very easily slipped two fingers inside his hot, pounding hole. He smirked up at his darling scientist. 

“You’re extremely tight, Flug. Is my tongue the only thing that’s been up here~?” He asked. Flug shrugged. 

“W...Well...depends. I’ve put whiteboard markers up there, just to test something.” Black Hat snickered. 

“Oh, you’re NASTY. I’ll probably be taking those for personal use when we’re done here~” He teased. The demon thrusted his fingers into Flug surprisingly gently, his pace decent. He would occasionally curl them, causing Flug to squeal. 

“M-Mm-!” It was starting to hurt slightly from the curling, but it was a good hurt in his opinion. 

Black Hat began to pay attention to his poor, ignored clit. He popped it right in his mouth and began to suck and lick it, loving how much he had to work with. Flug was an utter mess. He was shaking, moaning, drooling, just an all around absolute mess of hormones. The chair was slick with the mixture of his pussy juices and his boss’s salvia. His second orgasm hit him even harder than the first, almost giving him the feeling of blacking out. 

“Sh-Shit~! Shit~!” Flug yelped out as he came. His walls clenched tightly around his boss’s fingers, so much so he wouldn’t have been able to pull them out if he’d tried in that moment. When he was able, Black Hat slowly pulled his fingers out, watching the juices dribble out along with him. He sat up and began to suck on his fingers, savoring Flug’s taste. Next, came him cleaning up Flug himself. His rough, almost cat-like tongue lapped the dazed scientist clean, licking up any of the juices that remained. 

“Flug? Flug, look at me.”

The scientist looked down at his boss after a moment of trying to process what he’d just said. The demon was smirking, his large fangs exposed. 

“Y...Yes?”

“You promise me you’re gonna work~?” Black Hat squeezed his thigh to emphasize his point. Flug whined and nodded. 

“Absolutely, sir...” 

Black Hat stood up, dusting off himself. Flug couldn’t help but stare at the bulge in his tight dress pants. He assumed his boss was hung, but...holy hell. The demon scoffed. 

“I can see you staring, you harlot.” He plucked the markers off the whiteboard and smirked, “Maybe some day, you can have it~” 

“God, please, sir-“ Flug spit out without much thought. His boss chuckled. 

“Oh, Flug. If I’d known you were this into me, I’d have been doing this long ago~” And with that, the demon was gone, and Flug was left to clean up the mess that remained. He shakily got himself dressed and began to wipe down the seat with a rag he always had spares of. If all he had to do was misbehave a little to get treated like that...well, he was down to rebel a bit.


	2. Second Time’s a Charm

**Summary for the Chapter:**

> Flug finally has a dream come true.

**Notes for the Chapter:**

> Heyooooo sorry for not updating in a while y’all. Animal Crossing has consumed my life lmao oops. Also I came out online as a trans guy so woot. Anyway, here’s another self indulgent hormone fest.

The days passed, and Flug was still reeling from the experience he had with his boss. His mind was consumed by it most of the time, and he wasn’t particularly faking his slaking on work. He would spend most of the time fantasizing about that tongue deep inside him, those teeth just centimeters from penetrating his flesh. At night, he would usually put himself to sleep with an orgasm, imagining the demon fucking him deep and hard. 

Black Hat, however, was getting quite fed up with Flug’s lack of improvement. He was slipping? He didn’t understand it. And now he was late coming to the meeting he called him to? The demon tapped his claws against his desk, awaiting Flug’s arrival. The scientist sheepishly peeked in after a few minutes. 

“You...wanted to see me, s-“

“Oh, goddamn you Flug. Just step in. Don’t waste my time.” He growled. Flug quickly darted in, shutting the door behind him. 

“What seems to be the issue, sir?”

“Your performance has been only getting worse! You haven’t made any progress on the device in days. What happened?!”

“W-Well, uh, you see-“

“Is it that bear? Is he too much of a burden to your workload?” 

“What? No! Of course not!”

“Then what is your issue, Flug?” 

“Erm...” The scientist didn’t answer. He simply trailed off, sweat beginning to form on his body. He was heating up. Obviously, he couldn’t just say it. He couldn’t just say “I really just want your cock, sir.”

“Well?”

“Well, what?”

“What’s your issue? Are you growing ill? Because I will not tolerate human sicknesses near me, and I WILL happily lock you in the basement until it goes away.”

“S-Sir, I’m not sick! I-I just...” 

Black Hat smirked. He knew what Flug’s problem was. He could smell his dampening cunt quite easily. Having such a strong sense of smell came in handy to tease those he was interested in sexually. 

“Lock the door, Flug.”

“Wh-What?”

“You heard me. We don’t need Demencia or that bear waddling in.” 

Flug did as instructed. He then turned to Black Hat, his head cocked. He looked so innocent to Black Hat. 

“Now, I know what your little issue is. You’re constantly horny. Have you considered most of us just work through it? That we don’t just constantly fantasize and jerk off? That we hold it in until later?” The demon slouched back slightly, his hips pointed forward more. It was now clear that he had a bit of an erection. Flug immediately looked away, not wanting to be rude and stare. 

“E-Er...yes, sir...”

“Do you see where I’m going with this, Flug?”

“N...Not really?”

The demon sneered. One hand was rubbing the slowly forming bulge, the other tapping his claws on the desk. He stared Flug down, challenging him. 

“I’d like you to relieve me, Flug~” 

Flug couldn’t believe what he was hearing. Sucking his boss’s cock? Or maybe actually having sex with him? It was a dream come true. He didn’t even process walking over to his boss and getting on his knees before him. He tipped the bag up over his mouth, and Black Hat promptly pushed an ungloved finger inside of it. Flug coughed slightly in surprise. He allowed his boss to essentially finger his mouth, gagging occasionally when he would go near his throat. He was a drooling mess as his boss added another finger to the mix. Out of instinct, he began to suck on Black Hat’s fingers, taking his boss by surprise. 

“Oh my, Flug. You’re certainly still a harlot, I see.” He chuckled a little. He pulled his fingers out, the salvia trail not breaking for a moment. Flug panted slightly, peering up at Black Hat with excited eyes. 

“One could say that...” Flug replied. He watched as his boss unzipped those tight dress pants and fumble with his boxers slightly. Black Hat growled in annoyance before just pulling everything off below the waist. 

For one, his body was completely smooth. He was void of any body hair anywhere, a complete 180 from Flug. Flug could just barely make out a small amount of muscle under his shirt, but just barely. His boss was a slender creature through and through. Aside from one thing, however.

Where a normal human penis would be was instead a slimy, thick tentacle. Flug gulped slightly. It clearly wasn’t fully erect, yet was quite a bit larger than an average, erect human penis. The appendage thickened at the base, and a sheath was present. So THAT’S where he hid it...

Flug anxiously reached forward, before Black Hat growled sharply at him. 

“Take those gloves off before touching it! They’re cold!” He snapped. Flug quickly flung them off before gripping the tentacle at the base. He wasn’t sure if he should be more gentle- or more rough? He assumed Black Hat would scold him for doing something wrong. He hummed softly as he felt the organ with his other hand. It felt so hot and smooth, and of course, slimy. The thin tip attempted to wrap around his fingers at one point, earning Flug a chuckle from his boss. 

“It likes you, Flug~” He teased. Flug averted his eyes a bit, his red face pounding with heat. 

“I-I guess so, sir...” He murmured. He rubbed the tentacle softly, more curious about it than anything. He could feel internal ridges, he presumed they helped keep it erect. As he felt his boss up, the tentacle grew slimier, and of course harder. Black Hat grunted slightly.

“Don’t be a tease, Flug. Hurry it up.” The tip of his tentacle oozed clear precum, signaling his need. Flug nodded, gripped the appendage harder, and popped the tip in his mouth. 

The taste was...well, not what he expected. He expected a salty taste, but was greeted with a taste more akin to a mild sour candy. He was a little confused, but he wasn’t complaining. He was in heaven. He was desperate to please his boss. He took in a bit more than he could handle, and promptly pulled back to gag. Black Hat snickered. 

“Hey, now, don’t bite off more than you can chew. Okay, don’t bite it at all. Please.” Flug giggled nervously before resuming. 

He was obviously very unexperienced, but knew enough about cis male biology to know what to do, vaguely. He focused his tongue on the tip, hoping like humans, it was most sensitive. He swirled his tongue about, drooling without care. He peered up at Black Hat, focusing on the tip only. The taste was growing on him quite a lot as more of that thick pre poured out. Black Hat shifted slightly, a small groan escaping his mouth. 

“Mm...c’mon, use your hands on it more. If you can’t take more than that, you can at least put your hands to work.” Flug nodded, now stroking his boss with one hand, and rubbing himself through his jeans with the other. He felt so vile for being so turned on by just sucking him off, but who could help that? Everyone wanted Black Hat, and he was getting him. As far as he knew, his boss didn’t get involved sexually with such low ranking villains such as himself. Well, he was quite high ranking, but Black Hat had high standards. Either way, he was getting what most could only dream of. He whined softly. 

The demon, on the other hand, was having to resist making noise or showing too much pleasure. He didn’t want Flug to think he was on the verge of melting. Flug’s mouth was so hot, so wet, so tight... he so wanted to pin Flug’s head against the desk and fuck his tight little throat, but he knew he needed to resist, as to not scare Flug off entirely. He nipped at his own palm slightly, closing his eyes and groaning slightly. 

“Is this...your first time?” He panted out. Flug looked back up at him with those piercing eyes. 

“Y-Yes...why? A-Am I doing bad?” He asked nervously. Black Hat shook his head quickly. 

“No no, not at all. I’m...rather impressed,” He shifted again, his legs tensing. He was trying so fucking hard to be calm, “As a pointer, however, I fucking love having my sheath played with.” He knew if Flug started touching it, his calm, uninterested facade would be broken, but fuck, he needed even more. He wanted to be greedy and just get it all. 

Flug nodded before moving away from his tip. He moved his hand to that tender, writhing tip and began to lick and suck his sheath. That was it. That was game over. 

The demon couldn’t hold back, growling loudly in pleasure. He wrapped his legs around Flug’s neck, pushing him in closer to him. Flug adored the smell Black Hat gave off; a mix of expensive cologne and natural musk he presumed was a demon thing. Flug giggled a little from his boss’s sudden show of vulnerability. He hadn’t seen him in such a vulnerable state before, and he loved having him at his mercy. Black Hat whined slightly. 

“M...More...” He growled. The tentacle writhed against Flug’s cheek as he buried himself against the shaft, humming and drooling wildly. His hand was now down his boxers, quite fervently rubbing his clit. Honestly, he wasn’t sure who would cum first at that point. 

Black Hat was fully leaned back in his chair, absolutely melting below Flug. It had been so long since he’d received a blowjob and fuck, was this a good one. And from such an inexperienced man? He felt close to cumming already. He tilted his head back before snarling loudly in pleasure. He panted heavily, that long tongue only teasing Flug more. 

The demon’s orgasm was a sight to behold. He lurched forward, grabbing Flug’s head and pushing him against his sheath even more. He moaned out loudly, his moans sounding so akin to growls. Flug could feel the tentacle twitch hard against his cheek, and felt the cum splatter his hand and back. He moaned softly from the sight of seeing his boss so vulnerable. And he just kept cumming. Even when he was done actually producing semen, he still twitched and growled a bit. It took him a few minutes to completely recover from his high. He unwrapped his legs from Flug and sat up, coughing slightly. 

“Should’ve warned you, my species cums a lot, and for awhile. You’re a mess now.” He snickered. He peeled off his overcoat, tossing it aside. Flug was dazed slightly from everything he had just witnessed. Black Hat patted his lap slightly. 

“C’mere. I’ll give you something in return, for doing such an amazing job~ Get those pants and boxers off.” Flug shakily stood up, the heat between his thighs overwhelming. The pressure his cunt was feeling was beyond overwhelming. He couldn’t think straight at all, he just needed to cum. He did as told, shifting himself onto Black Hat’s lap carefully. The tentacle was growing a bit flaccid, but that didn’t stop Flug from pressing himself against the thick organ. He needed any kind of friction, and began to rut against the tentacle slightly. Black Hat raised a brow. 

“Flug, I’ll be empty for awhile. Trust me, you’re not getting any more out of that.” He pushed a finger between his cock and Flug’s pussy, which easily slipped into the wet hole unintentionally. Flug gasped slightly, relieved to feel something inside of him. His legs were shaky as he did his best to hold himself up. He was dripping all over his boss’s lap, but the demon didn’t seem to care. He just added another finger and got to work. 

Flug squirmed, trying to get Black Hat to go deeper. He didn’t bother trying to hide his moans. He just let them all out. He rutted hard against Black Hat’s hand, his throbbing clit desperate for relief. It didn’t take but a minute for Flug to cum. Liquids gushed forth, only creating a larger mess on the demon’s lap. Flug squealed out loudly as his orgasm hit him hard. He could barely even hold himself up as he came. He was addicted to this. 

And he needed more.


End file.
